Abstract
Proton transfers from protonated 1,8-bis(dialkylamino) naphthalenes to hydroxide ion are slow, largely because of strong intramolecular hydrogen bonds in the protonated amines. The results are discussed with reference to the general conclusion that the extent to which the rate of thermodynamically favourable proton transfer from an intramolecularly hydrogen bonded acid is lowered below the diffusion limited value gives a measure of the strength of the hydrogen bond. The several assumptions leading to this conclusion are described. The N....H....N hydrogen bond in 1,8-bis (dimethylamino)naphthalene which results in a lowering of rate of ca.105 is particularly strong and is probably an important factor in determining the unusual basicity of 1,8-bis(dimethylamino) naphthalene.
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